Advances in Heterocyclic Chemistry, Vol. 26 by A.R. Katritzky, A.J. Boulton (Eds.)

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By A.R. Katritzky, A.J. Boulton (Eds.)

(from preface)Volume 26 includes 3 chapters. C.A.Ramsden reports heterocy-clic betaines derived from 6-membered heteroaromatic earrings. those compounds were intensively studied during the last 10 years and feature no longer formerly been comprehensively reviewed. O. Meth-Cohn and B. Tarnowski summarize the chemistry of the thiocoumarins, a slightly ignored crew of heterocycles. ultimately, W. Friedrichsen has reviewed the chemistry of the benzo[r]furans which, not like the aza and thia analogs, haven't formerly been thought of during this sequence. right here back we've got a bunch of compounds the chemistry of which has complex significantly during the last decade.

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1 6 4 D. E. Ames, H. R. Ansari, A. D. G. France, A. C. Lovesey, B. Novitt, and R. Simpson, J . Chem. Soc. C, 3088 (1971). 165 D. E. Ames, S. Chandrasekhar. and R. Simpson, J . C . , Perkin 1, 2035 (1975). 1 6 6 G . M. Singerman, in “The Chemistry of Heterocyclic Compounds” (R. N. ). Vol. 27, p. 87. Wiley (Interscience), New York, 1973. lS4 Sec. B] 43 HETEROCYCLIC BETAINES of 4-hydroxycinnolines in alkaline media is a general route to the N-alkyl betaines 233. ' Evidence for this steric effect is provided by observation that, when using bulky alkyl groups, or with 8-substituted-4-hydroxycinnolines,almost exclusive formation of the mesomeric betaine (233) O C C U ~ S In.

Perkins I , 2054 (1972). N. Dennis, A. R. K. Parton, Chrm. Pharm. Bull. 23, 2899 (1975). " N. '* 32 [Sec. B CHRISTOPHER A. RAMSDEN isolated but aromatize spontaneously. 97 3. Isoquinolinium-4-aminides (178) Thermolysis of 1-cyclohexyl-6-(cyclohexylimino)la-phenylindano [ 1,2blaziridine (179; R' = Ph, R' = R4 = C 6 H l l , R 3 = H) in toluene or xylene at 135°C gives a deep purple solution of the isoquinolinium betaine 178 (R' = Ph, R' = R4 = C6H11, R3 = H). This valence tautomerism (179 -+ 178) is reversed by cooling or sunlight, but prolonged heating results in slow elimination of cyclohexene and formation of 1-phenyl-4-cyclohexylaminoisoquinoline.

Chew. Ges. 36, I169 (1903). W. Schneider and A. Pothmann, Ber. Dtsch. Chern. Ges. B 74, 471 (1941). A. Clam and H. Howitz, J . Prakl. C h m i . 56, 438 (1897). Sec. C] 53 HETEROCYCLIC BETAINES The triaryl compounds 290 (R = Ar) are prepared by condensation of 2-aminophenol with triarylpyrylium salts followed by treatment with alkali. 4s The mechanism of this unusual reaction has not yet been dstablished. ' 2. 217 3. 4-(Pyridinium)phenolates(297) These compounds (297) have interesting thermochromic and solvatochromic effects.

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